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Adaptive processes are fundamental to the human experience. This is true not only of adaptation to natural forces but to the technologies we create. Within information science and related fields, research into the processes that surround adaption to information tools often assumes a pro-adoption stance. When researchers privilege adoption, they may overlook complex interactions among values, information tool features, and individual and organizational choice. Towards addressing these limitations, the work reported here seeks to provide a richer understanding of the information tool adaptive process. Specifically, the work draws on Value Sensitive Design to investigate the adaptive process in two intentional communities striving to balance their use of tools with a set of core values related to sustainability. In the first phase of the investigation a community in the initial stages of development was studied for two years. For the second, shorter phase, a decade old community was studied for a period of weeks. Ethnographic methods were employed to document the adaptive process, the interactions of community members, and the information tools they used. Methods included participant observation, semi-structured interviews, and the collection of a range of community artifacts. Research outcomes include: (1) a rich description of information tool use outside of the workplace; (2) a categorization of information practices; (3) an analysis of tensions and barriers which emerge as a community's values conflict with their use of information tools; and (4) the development and assessment of methods to investigate the information tool adaptive process. Most broadly this work contributes to our larger understanding of challenges related to societal adaptation to and interaction with information tools. Findings from this investigation call into question previous claims that groups of individuals with strong value commitments can adapt their use of information tools to better support their values. In contrast, this work suggests that information tool interactions are particularly resilient to local, value based, adaptations. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]